title: Overcoming co-product inhibition in the nicotinamide independent asymmetric bioreduction of activated C=C-bonds using flavin-dependent ene-reductases.
abstract: Eleven flavoproteins from the old yellow enzyme family were found to catalyze the disproportionation ("dismutation") of conjugated enones. Incomplete conversions, which were attributed to enzyme inhibition by the co-product phenol could be circumvented via in situ co-product removal by scavenging the phenol using the polymeric adsorbent MP-carbonate. The optimized system allowed to reduce an alkene activated by ester groups in a "coupled-substrate" approach via nicotinamide-free hydrogen transfer with >90% conversion and complete stereoselectivity.
authors.affiliation: Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010, Graz, Austria.
authors.forename: Christoph K
authors.initials: CK
authors.lastname: Winkler
authors.forename: Dorina
authors.initials: D
authors.lastname: Clay
authors.forename: Esta
authors.initials: E
authors.lastname: van Heerden
authors.forename: Kurt
authors.initials: K
authors.lastname: Faber
mesh_terms: D000473:Alkanes / Q000378:metabolism*; D003067:Coenzymes / Q000378:metabolism*; D004138:Dinitrocresols / Q000378:metabolism*; D004791:Enzyme Inhibitors / Q000378:metabolism; D005420:Flavoproteins / Q000378:metabolism*; D009536:Niacinamide / Q000378:metabolism; D010084:Oxidation-Reduction; D010088:Oxidoreductases / Q000378:metabolism*; D019800:Phenol / Q000378:metabolism
chemical_list: D000473:Alkanes; D003067:Coenzymes; D004138:Dinitrocresols; D004791:Enzyme Inhibitors; D005420:Flavoproteins; C024132:4,6-dinitro-o-cresol; D009536:Niacinamide; D019800:Phenol; D010088:Oxidoreductases
keywords: disproportionation; ene-reductase; in situ co-product removal; old yellow enzyme